JP4625186B2 - アセチレンアルコールの製造方法およびその二次製品 - Google Patents
アセチレンアルコールの製造方法およびその二次製品 Download PDFInfo
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- JP4625186B2 JP4625186B2 JP2000600955A JP2000600955A JP4625186B2 JP 4625186 B2 JP4625186 B2 JP 4625186B2 JP 2000600955 A JP2000600955 A JP 2000600955A JP 2000600955 A JP2000600955 A JP 2000600955A JP 4625186 B2 JP4625186 B2 JP 4625186B2
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
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- 239000000203 mixture Substances 0.000 claims abstract description 152
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 74
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 239000002904 solvent Substances 0.000 claims abstract description 51
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 47
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims abstract description 38
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 35
- 150000001298 alcohols Chemical class 0.000 claims abstract description 22
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- 238000000034 method Methods 0.000 claims description 104
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- 239000012074 organic phase Substances 0.000 claims description 41
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 36
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
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- 238000000605 extraction Methods 0.000 claims description 11
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 10
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-butyl carbinol Natural products CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 7
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001299 aldehydes Chemical class 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 6
- COFFUYZBRGBAQS-FMIVXFBMSA-N (e)-6,10-dimethylundec-5-en-2-one Chemical compound CC(C)CCC\C(C)=C\CCC(C)=O COFFUYZBRGBAQS-FMIVXFBMSA-N 0.000 claims description 5
- XBDSNLZMMLMIIK-UHFFFAOYSA-N 6,11,14-trimethylpentadecan-2-one Chemical compound CC(C)CCC(C)CCCCC(C)CCCC(C)=O XBDSNLZMMLMIIK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001241 acetals Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000003472 neutralizing effect Effects 0.000 claims description 5
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 5
- 150000003333 secondary alcohols Chemical class 0.000 claims description 5
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 5
- SPPWGCYEYAMHDT-UHFFFAOYSA-N 1,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(C(C)C)C=C1 SPPWGCYEYAMHDT-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000000075 primary alcohol group Chemical group 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 150000001983 dialkylethers Chemical class 0.000 claims 3
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 abstract description 44
- 238000004821 distillation Methods 0.000 abstract description 19
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 13
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract description 11
- 150000004703 alkoxides Chemical class 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 20
- 238000000926 separation method Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- ZWNMRZQYWRLGMM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diol Chemical compound CC(C)(O)CCC(C)(C)O ZWNMRZQYWRLGMM-UHFFFAOYSA-N 0.000 description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 16
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- LBOHISOWGKIIKX-UHFFFAOYSA-M potassium;2-methylpropanoate Chemical compound [K+].CC(C)C([O-])=O LBOHISOWGKIIKX-UHFFFAOYSA-M 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- IHJUECRFYCQBMW-UHFFFAOYSA-N 2,5-dimethylhex-3-yne-2,5-diol Chemical compound CC(C)(O)C#CC(C)(C)O IHJUECRFYCQBMW-UHFFFAOYSA-N 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 8
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- 239000000243 solution Substances 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
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- 239000001257 hydrogen Substances 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
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- JQZGUQIEPRIDMR-UHFFFAOYSA-N 3-methylbut-1-yn-1-ol Chemical compound CC(C)C#CO JQZGUQIEPRIDMR-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
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- 229910017053 inorganic salt Inorganic materials 0.000 description 3
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- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- HNVRRHSXBLFLIG-UHFFFAOYSA-N 3-hydroxy-3-methylbut-1-ene Chemical compound CC(C)(O)C=C HNVRRHSXBLFLIG-UHFFFAOYSA-N 0.000 description 2
- DPLGXGDPPMLJHN-UHFFFAOYSA-N 6-Methylheptan-2-one Chemical compound CC(C)CCCC(C)=O DPLGXGDPPMLJHN-UHFFFAOYSA-N 0.000 description 2
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- 229920002266 Pluriol® Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
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- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 description 1
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- RAYSJZWIMVHXOA-UHFFFAOYSA-N 3,7,11-trimethyldodeca-1,6-dien-3-ol Chemical compound CC(C)CCCC(C)=CCCC(C)(O)C=C RAYSJZWIMVHXOA-UHFFFAOYSA-N 0.000 description 1
- IUDWWFNDSJRYRV-UHFFFAOYSA-N 3,7-dimethyloct-1-en-3-ol Chemical compound CC(C)CCCC(C)(O)C=C IUDWWFNDSJRYRV-UHFFFAOYSA-N 0.000 description 1
- USCSRAJGJYMJFZ-UHFFFAOYSA-N 3-methyl-1-butyne Chemical compound CC(C)C#C USCSRAJGJYMJFZ-UHFFFAOYSA-N 0.000 description 1
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- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
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- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
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- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- ICMWSAALRSINTC-UHFFFAOYSA-N penta-1,4-dien-3-ol Chemical compound C=CC(O)C=C ICMWSAALRSINTC-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
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- 238000012545 processing Methods 0.000 description 1
- FWLKYEAOOIPJRL-UHFFFAOYSA-N prop-1-yn-1-ol Chemical compound CC#CO FWLKYEAOOIPJRL-UHFFFAOYSA-N 0.000 description 1
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- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 239000002759 woven fabric Substances 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/172—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with the obtention of a fully saturated alcohol
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19907532.8 | 1999-02-22 | ||
DE19907532A DE19907532A1 (de) | 1999-02-22 | 1999-02-22 | Verfahren zur Herstellung von Acetylenalkoholen und deren Folgeprodukten |
PCT/EP2000/001425 WO2000050370A1 (de) | 1999-02-22 | 2000-02-22 | Verfahren zur herstellung von acetylenalkoholen und deren folgeprodukten |
Publications (2)
Publication Number | Publication Date |
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JP2002537367A JP2002537367A (ja) | 2002-11-05 |
JP4625186B2 true JP4625186B2 (ja) | 2011-02-02 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2000600955A Expired - Fee Related JP4625186B2 (ja) | 1999-02-22 | 2000-02-22 | アセチレンアルコールの製造方法およびその二次製品 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6956141B1 (zh) |
EP (1) | EP1161407B1 (zh) |
JP (1) | JP4625186B2 (zh) |
CN (1) | CN1213975C (zh) |
AT (1) | ATE258907T1 (zh) |
DE (2) | DE19907532A1 (zh) |
ES (1) | ES2215610T3 (zh) |
WO (1) | WO2000050370A1 (zh) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10123066A1 (de) | 2001-05-11 | 2002-11-14 | Basf Ag | Verfahren zur Herstellung von höheren alpha,beta-ungesättigten Alkoholen |
CN101234950B (zh) * | 2008-02-02 | 2010-12-29 | 泸州富邦化工有限公司 | 萃取及减压蒸馏法生产2,5-二甲基-2,5-己二醇工艺 |
KR101191122B1 (ko) * | 2009-01-20 | 2012-10-15 | 주식회사 엘지화학 | 고순도 노르말 부탄올 생산용 분리벽형 증류탑, 및 노르말 부탄올 증류방법 |
CN102355928B (zh) * | 2009-03-19 | 2014-03-12 | Lg化学株式会社 | 用于制备高纯度2-乙基己醇的分隔壁蒸馏塔和采用该分隔壁蒸馏塔的分馏方法 |
JP6134338B2 (ja) | 2012-02-29 | 2017-05-24 | バルーク エス.ブルームバーグ インスティテュート | B型肝炎ウイルス共有結合閉環状dna形成の阻害剤およびそれらの使用方法 |
RU2479565C1 (ru) * | 2012-03-07 | 2013-04-20 | Федеральное государственное бюджетное учреждение науки Иркутский институт химии им. А.Е. Фаворского Сибирского отделения Российской академии наук РАН (ИрИХ СО РАН) | Способ получения алкиларил (гетарил) этинилкарбинолов |
JP6226439B2 (ja) * | 2013-01-23 | 2017-11-08 | ディーエスエム アイピー アセッツ ビー.ブイ. | 2−アルキル−3−ブチン−2−オールの製造方法 |
WO2018033635A1 (en) | 2016-08-19 | 2018-02-22 | Nitto Belgium Nv | Preparation of tmthf |
CN107827711B (zh) * | 2017-10-31 | 2023-09-29 | 西南化工研究设计院有限公司 | 一种联产甲基丁炔醇和二甲基己炔二醇的系统及工艺 |
KR102434452B1 (ko) * | 2018-11-28 | 2022-08-19 | 주식회사 엘지화학 | 가교제 화합물의 제조 방법 |
CN110467519B (zh) * | 2019-09-16 | 2022-08-05 | 万华化学集团股份有限公司 | 一种乙炔化方法 |
CN113735685B (zh) * | 2021-09-27 | 2024-03-01 | 四川众邦新材料股份有限公司 | 联产二甲基己炔二醇和甲基丁炔醇的方法 |
CN113717031B (zh) * | 2021-09-27 | 2024-04-12 | 四川众邦新材料股份有限公司 | 一种联产四甲基十二炔二醇和二甲基庚炔醇的方法 |
CN113816835B (zh) * | 2021-09-27 | 2024-04-12 | 四川众邦新材料股份有限公司 | 一种联产二甲基癸炔二醇和甲基己炔醇的方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2385546A (en) * | 1943-11-05 | 1945-09-25 | Commercial Solvents Corp | Continuous process for the preparation of acetylenic alcohols |
FR950894A (fr) * | 1944-10-23 | 1949-10-10 | Distillers Co Yeast Ltd | Perfectionnements à la fabrication d'alcools acétyléniques |
US2488082A (en) * | 1944-10-23 | 1949-11-15 | Distillers Co Yeast Ltd | Manufacture of acetylenic alcohols |
DE2008675A1 (de) | 1970-02-25 | 1971-09-09 | Badische Anilin & Soda Fabrik AG, 6700 Ludwigshafen | Verfahren zur Herstellung von tertiären Acetylenglykolen durch Umsetzung von Acetylen mit Ketonen |
DE4220239C2 (de) * | 1992-06-20 | 1996-03-07 | Basf Ag | Mischvorrichtung |
US5444170A (en) | 1994-01-10 | 1995-08-22 | Air Products And Chemicals, Inc. | Hydrogenation of acetylenic compounds |
-
1999
- 1999-02-22 DE DE19907532A patent/DE19907532A1/de not_active Withdrawn
-
2000
- 2000-02-22 CN CNB008054339A patent/CN1213975C/zh not_active Expired - Fee Related
- 2000-02-22 US US09/913,979 patent/US6956141B1/en not_active Expired - Fee Related
- 2000-02-22 DE DE50005197T patent/DE50005197D1/de not_active Expired - Lifetime
- 2000-02-22 WO PCT/EP2000/001425 patent/WO2000050370A1/de active IP Right Grant
- 2000-02-22 JP JP2000600955A patent/JP4625186B2/ja not_active Expired - Fee Related
- 2000-02-22 AT AT00906367T patent/ATE258907T1/de not_active IP Right Cessation
- 2000-02-22 EP EP00906367A patent/EP1161407B1/de not_active Expired - Lifetime
- 2000-02-22 ES ES00906367T patent/ES2215610T3/es not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US6956141B1 (en) | 2005-10-18 |
ES2215610T3 (es) | 2004-10-16 |
DE50005197D1 (de) | 2004-03-11 |
JP2002537367A (ja) | 2002-11-05 |
DE19907532A1 (de) | 2000-08-31 |
EP1161407B1 (de) | 2004-02-04 |
WO2000050370A1 (de) | 2000-08-31 |
CN1213975C (zh) | 2005-08-10 |
ATE258907T1 (de) | 2004-02-15 |
EP1161407A1 (de) | 2001-12-12 |
CN1344239A (zh) | 2002-04-10 |
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